JP2014530813A5 - - Google Patents
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- Publication number
- JP2014530813A5 JP2014530813A5 JP2014535037A JP2014535037A JP2014530813A5 JP 2014530813 A5 JP2014530813 A5 JP 2014530813A5 JP 2014535037 A JP2014535037 A JP 2014535037A JP 2014535037 A JP2014535037 A JP 2014535037A JP 2014530813 A5 JP2014530813 A5 JP 2014530813A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- trifluoromethyl
- guanidine
- methyl
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 16
- -1 nitro, cyano, methyl Chemical group 0.000 claims 10
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 229910052740 iodine Inorganic materials 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000004122 cyclic group Chemical group 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- BEZGMANANMSUSQ-UHFFFAOYSA-N 2-(4,6-dimethylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC(C)=NC(N=C(N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 BEZGMANANMSUSQ-UHFFFAOYSA-N 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- DVIJFJSZZNOTLP-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC(C)=CC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1 DVIJFJSZZNOTLP-UHFFFAOYSA-N 0.000 claims 4
- AYHNNQRJIFYJCG-UHFFFAOYSA-N 1-(3-nitrophenyl)-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound [O-][N+](=O)C1=CC=CC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1 AYHNNQRJIFYJCG-UHFFFAOYSA-N 0.000 claims 4
- SWYDMSLWYYPTPB-UHFFFAOYSA-N 1-phenyl-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=CC=C1 SWYDMSLWYYPTPB-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- JPPYJNPDNWUKRP-UHFFFAOYSA-N 2-(2-methylphenyl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F JPPYJNPDNWUKRP-UHFFFAOYSA-N 0.000 claims 3
- ZOBFMPILPJICCH-UHFFFAOYSA-N 2-(5-methylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound N1=CC(C)=CN=C1NC(=N)NC1=CC=CC=C1C(F)(F)F ZOBFMPILPJICCH-UHFFFAOYSA-N 0.000 claims 3
- DMIYZPSMBHPOFW-UHFFFAOYSA-N 2-[4-methyl-6-(trifluoromethyl)pyrimidin-2-yl]-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC(C(F)(F)F)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 DMIYZPSMBHPOFW-UHFFFAOYSA-N 0.000 claims 3
- 210000004027 cells Anatomy 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- XXTZFJFZTATUMB-UHFFFAOYSA-N 1-(1H-pyrrol-3-yl)-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CNC=C1 XXTZFJFZTATUMB-UHFFFAOYSA-N 0.000 claims 2
- SKVUMDVUYSDPAS-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=NC(C)=CC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1 SKVUMDVUYSDPAS-UHFFFAOYSA-N 0.000 claims 2
- MIUUHNWKPYSUPS-UHFFFAOYSA-N 1-(2-aminophenyl)-2-(4,6-dimethylpyrimidin-2-yl)guanidine Chemical compound CC1=CC(C)=NC(NC(=N)NC=2C(=CC=CC=2)N)=N1 MIUUHNWKPYSUPS-UHFFFAOYSA-N 0.000 claims 2
- KFBZRMAGUJAZAK-UHFFFAOYSA-N 1-(2-nitrophenyl)-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F KFBZRMAGUJAZAK-UHFFFAOYSA-N 0.000 claims 2
- VJYPBLYCAHOEMI-UHFFFAOYSA-N 1-(4-amino-2-methylquinolin-7-yl)-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound C=1C2=NC(C)=CC(N)=C2C=CC=1NC(=N)NC1=CC=CC=C1C(F)(F)F VJYPBLYCAHOEMI-UHFFFAOYSA-N 0.000 claims 2
- XQLOKGAQDIBOFN-UHFFFAOYSA-N 1-(4-nitrophenyl)-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F XQLOKGAQDIBOFN-UHFFFAOYSA-N 0.000 claims 2
- YFWDUFCRFPZCGX-UHFFFAOYSA-N 1-(furan-3-yl)-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=COC=C1 YFWDUFCRFPZCGX-UHFFFAOYSA-N 0.000 claims 2
- KPEAAWKORXHPDH-UHFFFAOYSA-N 1-[2-(dibutylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCCCN(CCCC)S(=O)(=O)C1=CC=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F KPEAAWKORXHPDH-UHFFFAOYSA-N 0.000 claims 2
- RLVCWMDLZDMRKI-UHFFFAOYSA-N 1-[2-(diethylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F RLVCWMDLZDMRKI-UHFFFAOYSA-N 0.000 claims 2
- XFRCPKKRUCPBCP-UHFFFAOYSA-N 1-[2-(dimethylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CN(C)S(=O)(=O)C1=CC=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F XFRCPKKRUCPBCP-UHFFFAOYSA-N 0.000 claims 2
- GQJUYBBCGFMMMP-UHFFFAOYSA-N 1-[2-(dipropylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F GQJUYBBCGFMMMP-UHFFFAOYSA-N 0.000 claims 2
- WXIMVZCBEBEJSJ-UHFFFAOYSA-N 1-[3-(dibutylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCCCN(CCCC)S(=O)(=O)C1=CC=CC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1 WXIMVZCBEBEJSJ-UHFFFAOYSA-N 0.000 claims 2
- HMKUOKPOUHLVKN-UHFFFAOYSA-N 1-[3-(diethylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1 HMKUOKPOUHLVKN-UHFFFAOYSA-N 0.000 claims 2
- BYEPCRCVOBSOHO-UHFFFAOYSA-N 1-[3-(dimethylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CN(C)S(=O)(=O)C1=CC=CC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1 BYEPCRCVOBSOHO-UHFFFAOYSA-N 0.000 claims 2
- UHMVAXXPILSDMG-UHFFFAOYSA-N 1-[3-(dipropylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=CC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1 UHMVAXXPILSDMG-UHFFFAOYSA-N 0.000 claims 2
- BEFHAPVDGXTCIW-UHFFFAOYSA-N 1-[4-(dibutylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound C1=CC(S(=O)(=O)N(CCCC)CCCC)=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F BEFHAPVDGXTCIW-UHFFFAOYSA-N 0.000 claims 2
- MXFZNCYFKNYNKH-UHFFFAOYSA-N 1-[4-(diethylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F MXFZNCYFKNYNKH-UHFFFAOYSA-N 0.000 claims 2
- SOPDWXLTDFWWDJ-UHFFFAOYSA-N 1-[4-(dimethylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F SOPDWXLTDFWWDJ-UHFFFAOYSA-N 0.000 claims 2
- QKTUODUPXXKSCD-UHFFFAOYSA-N 1-[4-(dipropylsulfamoyl)phenyl]-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1NC(=N)NC1=CC=CC=C1C(F)(F)F QKTUODUPXXKSCD-UHFFFAOYSA-N 0.000 claims 2
- GUMZSGOUHCRFKB-UHFFFAOYSA-N 1-pyridin-3-yl-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=CN=C1 GUMZSGOUHCRFKB-UHFFFAOYSA-N 0.000 claims 2
- OIQSWMCDFLFXJS-UHFFFAOYSA-N 1-pyridin-4-yl-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=NC=C1 OIQSWMCDFLFXJS-UHFFFAOYSA-N 0.000 claims 2
- XIFXDYRWWNDRAN-UHFFFAOYSA-N 1-pyrimidin-5-yl-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CN=CN=C1 XIFXDYRWWNDRAN-UHFFFAOYSA-N 0.000 claims 2
- LLNSEXNTRYZPDD-UHFFFAOYSA-N 1-quinolin-7-yl-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=C(C=CC=N2)C2=C1 LLNSEXNTRYZPDD-UHFFFAOYSA-N 0.000 claims 2
- DSDRNKAHSLTIJH-UHFFFAOYSA-N 1-thiophen-3-yl-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CSC=C1 DSDRNKAHSLTIJH-UHFFFAOYSA-N 0.000 claims 2
- ATHMSZNYPIELQJ-UHFFFAOYSA-N 2-(1,2-oxazol-5-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=NO1 ATHMSZNYPIELQJ-UHFFFAOYSA-N 0.000 claims 2
- AIKMDLHSGPJBPF-UHFFFAOYSA-N 2-(1,3-oxazol-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=NC=CO1 AIKMDLHSGPJBPF-UHFFFAOYSA-N 0.000 claims 2
- VTPDYKSGBZLXBG-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=NC=CS1 VTPDYKSGBZLXBG-UHFFFAOYSA-N 0.000 claims 2
- SGHVNVYGIRVVMW-UHFFFAOYSA-N 2-(1H-benzimidazol-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=NC2=CC=CC=C2N1 SGHVNVYGIRVVMW-UHFFFAOYSA-N 0.000 claims 2
- MCIWWALWCUPPHO-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=NC=CN1 MCIWWALWCUPPHO-UHFFFAOYSA-N 0.000 claims 2
- JXHTXWBEHLLOPH-UHFFFAOYSA-N 2-(1H-pyrrol-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=CN1 JXHTXWBEHLLOPH-UHFFFAOYSA-N 0.000 claims 2
- KCGKTBGOZQEWRM-UHFFFAOYSA-N 2-(3,4-dimethyl-1,2-oxazol-5-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=NOC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1C KCGKTBGOZQEWRM-UHFFFAOYSA-N 0.000 claims 2
- WLNMRWUZWYLGAI-UHFFFAOYSA-N 2-(4,6-diaminopyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound NC1=CC(N)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 WLNMRWUZWYLGAI-UHFFFAOYSA-N 0.000 claims 2
- WUHUVIRLZBFKDC-UHFFFAOYSA-N 2-(4,6-dichloropyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=NC(Cl)=CC(Cl)=N1 WUHUVIRLZBFKDC-UHFFFAOYSA-N 0.000 claims 2
- OJNVEKAGZIDREM-UHFFFAOYSA-N 2-(4,6-dicyanopyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=NC(C#N)=CC(C#N)=N1 OJNVEKAGZIDREM-UHFFFAOYSA-N 0.000 claims 2
- LVRQRWDSDUGNJN-UHFFFAOYSA-N 2-(4,6-difluoropyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC1=CC(F)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 LVRQRWDSDUGNJN-UHFFFAOYSA-N 0.000 claims 2
- FNXNPLCKXXQPBX-UHFFFAOYSA-N 2-(4,6-dimethylpyridin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC(C)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1 FNXNPLCKXXQPBX-UHFFFAOYSA-N 0.000 claims 2
- ZAJKQVWBTXEGJM-UHFFFAOYSA-N 2-(4,6-dimethylpyrimidin-2-yl)-1-(3-ethylphenyl)guanidine Chemical compound CCC1=CC=CC(NC(=N)NC=2N=C(C)C=C(C)N=2)=C1 ZAJKQVWBTXEGJM-UHFFFAOYSA-N 0.000 claims 2
- QTSBNBBUTPPZRT-UHFFFAOYSA-N 2-(4-butyl-6-methylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCCCC1=CC(C)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 QTSBNBBUTPPZRT-UHFFFAOYSA-N 0.000 claims 2
- CVMBRONFKSNQEI-UHFFFAOYSA-N 2-(4-chloro-6-methylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC(Cl)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 CVMBRONFKSNQEI-UHFFFAOYSA-N 0.000 claims 2
- QKFZFLHXODDBJW-UHFFFAOYSA-N 2-(4-cyano-6-methylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC(C#N)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 QKFZFLHXODDBJW-UHFFFAOYSA-N 0.000 claims 2
- PYJRCCBGSPPRIW-UHFFFAOYSA-N 2-(4-ethyl-6-methylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCC1=CC(C)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 PYJRCCBGSPPRIW-UHFFFAOYSA-N 0.000 claims 2
- XHSLGHNEVDFQTA-UHFFFAOYSA-N 2-(4-fluoro-6-methylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC(F)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 XHSLGHNEVDFQTA-UHFFFAOYSA-N 0.000 claims 2
- VQDZFUPPAVAWQJ-UHFFFAOYSA-N 2-(4-fluoropyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC1=CC=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 VQDZFUPPAVAWQJ-UHFFFAOYSA-N 0.000 claims 2
- UGJOQPDLXZMDJB-UHFFFAOYSA-N 2-(4-methyl-6-propan-2-ylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC(C)C1=CC(C)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 UGJOQPDLXZMDJB-UHFFFAOYSA-N 0.000 claims 2
- WAPDPUYTPMNRDM-UHFFFAOYSA-N 2-(4-methyl-6-propylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCCC1=CC(C)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 WAPDPUYTPMNRDM-UHFFFAOYSA-N 0.000 claims 2
- YKQQUSKGNHYMOJ-UHFFFAOYSA-N 2-(4-methylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 YKQQUSKGNHYMOJ-UHFFFAOYSA-N 0.000 claims 2
- SIRSLOUDAUECOM-UHFFFAOYSA-N 2-(4-tert-butyl-6-methylpyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC(C(C)(C)C)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 SIRSLOUDAUECOM-UHFFFAOYSA-N 0.000 claims 2
- INJNHRBGTWBHQT-UHFFFAOYSA-N 2-(5-fluoropyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound N1=CC(F)=CN=C1NC(=N)NC1=CC=CC=C1C(F)(F)F INJNHRBGTWBHQT-UHFFFAOYSA-N 0.000 claims 2
- PDFOAAMZYZAWIN-UHFFFAOYSA-N 2-(6-methyl-4-oxo-1H-pyrimidin-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound N1C(C)=CC(=O)N=C1\N=C(\N)NC1=CC=CC=C1C(F)(F)F PDFOAAMZYZAWIN-UHFFFAOYSA-N 0.000 claims 2
- OVMMJLFXNXLTJQ-UHFFFAOYSA-N 2-(furan-2-yl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=CO1 OVMMJLFXNXLTJQ-UHFFFAOYSA-N 0.000 claims 2
- ICYQJUSKWXBAOO-UHFFFAOYSA-N 2-[4,6-bis(trifluoromethyl)pyrimidin-2-yl]-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=NC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=N1 ICYQJUSKWXBAOO-UHFFFAOYSA-N 0.000 claims 2
- TWZKJBDDIXUSBP-UHFFFAOYSA-N 2-[4-[(4-amino-2-methylquinolin-7-yl)amino]pyrimidin-2-yl]-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound C=1C2=NC(C)=CC(N)=C2C=CC=1NC(N=1)=CC=NC=1NC(=N)NC1=CC=CC=C1C(F)(F)F TWZKJBDDIXUSBP-UHFFFAOYSA-N 0.000 claims 2
- HRQVDDCXOPDENC-UHFFFAOYSA-N 2-butyl-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCCCNC(=N)NC1=CC=CC=C1C(F)(F)F HRQVDDCXOPDENC-UHFFFAOYSA-N 0.000 claims 2
- GRXLZYAFMRMBHJ-UHFFFAOYSA-N 2-ethyl-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCNC(=N)NC1=CC=CC=C1C(F)(F)F GRXLZYAFMRMBHJ-UHFFFAOYSA-N 0.000 claims 2
- OZHGTLHWXKLEBJ-UHFFFAOYSA-N 2-methyl-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CNC(=N)NC1=CC=CC=C1C(F)(F)F OZHGTLHWXKLEBJ-UHFFFAOYSA-N 0.000 claims 2
- DNQSRAPLLXYEQY-UHFFFAOYSA-N 2-propyl-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CCCNC(=N)NC1=CC=CC=C1C(F)(F)F DNQSRAPLLXYEQY-UHFFFAOYSA-N 0.000 claims 2
- XOXKJVLQWPQMKZ-UHFFFAOYSA-N 2-pyridin-2-yl-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=CC=N1 XOXKJVLQWPQMKZ-UHFFFAOYSA-N 0.000 claims 2
- TVZDGINLVXCQEH-UHFFFAOYSA-N 2-pyrimidin-2-yl-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=NC=CC=N1 TVZDGINLVXCQEH-UHFFFAOYSA-N 0.000 claims 2
- UZGKTFVPFCIMLO-UHFFFAOYSA-N 2-pyrimidin-4-yl-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=NC=N1 UZGKTFVPFCIMLO-UHFFFAOYSA-N 0.000 claims 2
- UFPSRSISFBVWBR-UHFFFAOYSA-N 2-thiophen-2-yl-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1=CC=CS1 UFPSRSISFBVWBR-UHFFFAOYSA-N 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 229940088597 Hormone Drugs 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000005556 hormone Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 230000002062 proliferating Effects 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- IXZXFWYQKMZGJR-UHFFFAOYSA-N 2-[2-(trifluoromethyl)phenyl]guanidine Chemical group NC(=N)NC1=CC=CC=C1C(F)(F)F IXZXFWYQKMZGJR-UHFFFAOYSA-N 0.000 claims 1
- 208000003200 Adenoma Diseases 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 208000009458 Carcinoma in Situ Diseases 0.000 claims 1
- 206010058314 Dysplasia Diseases 0.000 claims 1
- 210000004696 Endometrium Anatomy 0.000 claims 1
- 206010016629 Fibroma Diseases 0.000 claims 1
- 208000005017 Glioblastoma Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010020118 Histiocytosis Diseases 0.000 claims 1
- 210000002510 Keratinocytes Anatomy 0.000 claims 1
- 210000003734 Kidney Anatomy 0.000 claims 1
- 206010024324 Leukaemias Diseases 0.000 claims 1
- 210000004185 Liver Anatomy 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010061232 Lymphoproliferative disease Diseases 0.000 claims 1
- 206010025650 Malignant melanoma Diseases 0.000 claims 1
- 206010054949 Metaplasia Diseases 0.000 claims 1
- 210000002200 Mouth Mucosa Anatomy 0.000 claims 1
- 206010028576 Myeloproliferative disease Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000002154 Non-Small-Cell Lung Carcinoma Diseases 0.000 claims 1
- 108009000071 Non-small cell lung cancer Proteins 0.000 claims 1
- 210000001672 Ovary Anatomy 0.000 claims 1
- 210000000496 Pancreas Anatomy 0.000 claims 1
- 208000006994 Precancerous Condition Diseases 0.000 claims 1
- 210000002307 Prostate Anatomy 0.000 claims 1
- 102100002253 RAC1 Human genes 0.000 claims 1
- 101700023645 RAC1 Proteins 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 208000006641 Skin Disease Diseases 0.000 claims 1
- 206010041823 Squamous cell carcinoma Diseases 0.000 claims 1
- 210000001744 T-Lymphocytes Anatomy 0.000 claims 1
- 210000001550 Testis Anatomy 0.000 claims 1
- 210000003932 Urinary Bladder Anatomy 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N carbodiimide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- 230000001684 chronic Effects 0.000 claims 1
- 230000000112 colonic Effects 0.000 claims 1
- 230000001419 dependent Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000011523 endocrine gland cancer Diseases 0.000 claims 1
- 230000002496 gastric Effects 0.000 claims 1
- 200000000028 growth disorder Diseases 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 201000011066 hemangioma Diseases 0.000 claims 1
- 230000002489 hematologic Effects 0.000 claims 1
- 201000008298 histiocytosis Diseases 0.000 claims 1
- 230000002390 hyperplastic Effects 0.000 claims 1
- 230000002757 inflammatory Effects 0.000 claims 1
- 230000003902 lesions Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated Effects 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 230000015689 metaplastic ossification Effects 0.000 claims 1
- 101700037472 nhr-6 Proteins 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 201000007196 sexual disease Diseases 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
Claims (15)
の化合物もしくはその塩、又はその立体異性型の何れか又はこれらの混合物
(式中、
R1及びR1’は独立に、H、(C1〜C4)アルキル、CF3、F、Cl、Br、I、−CN、OH、NH2、−OCH3及びNO2からなる群から選択され;但し、R1及びR1’の少なくとも一つはH以外であり;
Aは直鎖もしくは分枝(C1〜C6)アルキル又は1〜2個の環を有する既知の炭素環もしくは複素環系の一つから選択される基であり、前記環系を形成する前記環の各々は、
5〜7員を有し、各員は独立に、C、N、O、S、CH、CH2、NHから選択され、
飽和、部分不飽和又は芳香族であり;
AはH、ハロゲン、ニトロ、シアノ、直鎖もしくは分枝(C1〜C6)アルキル、ハロ−(C1〜C6)アルキル、直鎖もしくは分枝(C2〜C6)アルケニル、−OR2、−COR2、−COOR2、−OC(O)R2、−C(O)NR3R4、−NR3R4、−R5NHR6、−SR2、−SO−R2、−SO2−R2及び−SO2NR3R4からなる群から選択される一又は複数の基で置換されており;
各R2は独立に、H又は直鎖もしくは分枝(C1〜C4)アルキルを表し、
各R3は独立に、H又は直鎖もしくは分枝(C1〜C4)アルキルを表し、
各R4は独立に、H、直鎖もしくは分枝(C1〜C6)アルキル、フェニル、ピリジン又はキノリンを表し;フェニル、ピリジン及びキノリン環系は、H、直鎖もしくは分枝(C1〜C4)アルキル、及びNH2から選択される一又は複数の基で置換されており;
R5及びR6は独立に、H、直鎖もしくは分枝(C1〜C4)アルキルから選択される)であって、Rho−GTPアーゼ細胞タンパク質がRac1であり、疾患が、胃腸又は結腸直腸管、肝臓、膵臓、腎臓、膀胱、前立腺、子宮内膜、卵巣、精巣の前癌状態;異形成;化生;癌、メラノーマ、異形成口腔粘膜、浸潤性口腔癌、小細胞及び非小細胞肺癌、ホルモン依存性乳癌、ホルモン非依存性乳癌、移行扁平上皮細胞癌、神経芽細胞腫、神経膠腫、神経膠芽腫、星状細胞腫を含む神経悪性腫瘍、骨肉種、軟部肉腫、血管腫、内分泌腫瘍、白血病、リンパ腫及び他の骨髄増殖性及びリンパ増殖性疾患を含む血液系新形成、上皮内癌、過形成病変、腺腫、線維腫、組織球増殖症、慢性炎症性増殖性疾患、血管増殖性疾患及びウイルス誘発増殖性疾患、ケラチノサイト及び/又はT細胞の過剰増殖を特徴とする皮膚疾患からなる群から選択される増殖性疾患である、化合物もしくはその塩、又はその立体異性型の何れか又はこれらの混合物。 Formula (I) for use in the treatment of conditions mediated by Rho-GTPase cell proteins
Or a salt thereof, or a stereoisomeric form thereof or a mixture thereof (wherein
R 1 and R 1 ′ are independently from the group consisting of H, (C 1 -C 4 ) alkyl, CF 3 , F, Cl, Br, I, —CN, OH, NH 2 , —OCH 3 and NO 2. Provided that at least one of R 1 and R 1 ′ is other than H;
A is a group selected from linear or branched (C 1 -C 6 ) alkyl or one of the known carbocyclic or heterocyclic systems having 1 to 2 rings, which forms said ring system Each of the rings
Has a 5- to 7-membered, independently each member is selected C, N, O, S, CH, from CH 2, NH,
Saturated, partially unsaturated or aromatic;
A is H, halogen, nitro, cyano, linear or branched (C 1 ~C 6) alkyl, halo - (C 1 ~C 6) alkyl, linear or branched (C 2 ~C 6) alkenyl, - OR 2, -COR 2, -COOR 2 , -OC (O) R 2, -C (O) NR 3 R 4, -NR 3 R 4, -R 5 NHR 6, -SR 2, -SO-R 2 Substituted with one or more groups selected from the group consisting of: —SO 2 —R 2 and —SO 2 NR 3 R 4 ;
Each R 2 independently represents H or linear or branched (C 1 -C 4 ) alkyl;
Each R 3 independently represents H or linear or branched (C 1 -C 4 ) alkyl;
Each R 4 independently represents H, linear or branched (C 1 -C 6 ) alkyl, phenyl, pyridine or quinoline; the phenyl, pyridine and quinoline ring systems are H, linear or branched (C 1 -C 4) alkyl, and is substituted with one or more groups selected from NH 2;
R 5 and R 6 are independently selected from H, linear or branched (C 1 -C 4 ) alkyl) , the Rho-GTPase cell protein is Rac1, and the disease is gastrointestinal or colonic Precancerous condition of rectal tube, liver, pancreas, kidney, bladder, prostate, endometrium, ovary, testis; dysplasia; metaplasia; cancer, melanoma, dysplastic oral mucosa, invasive oral cancer, small cells and non-small Cell lung cancer, hormone-dependent breast cancer, hormone-independent breast cancer, transitional squamous cell carcinoma, neuroblastoma, glioma, glioblastoma, neuromalignant tumors including astrocytoma, osteosarcoma, soft tissue sarcoma, Hematological neoplasia, including hemangiomas, endocrine tumors, leukemias, lymphomas and other myeloproliferative and lymphoproliferative diseases, carcinoma in situ, hyperplastic lesions, adenomas, fibromas, histiocytosis, chronic inflammatory growth Disease, vascular proliferative disease and virus-induced increase Proliferative disease selected sexual disorders, a hyperproliferation of keratinocytes and / or T cells from the group consisting of skin disorders characterized, compound or a salt thereof, or any or a mixture of these stereoisomers form.
から選択される環系であり、
Aが請求項1に記載される一又は複数の基で置換されており、波線が環と隣接窒素の結合の点を意味する、請求項1に記載の使用のための化合物。 A is
A ring system selected from
2. A compound for use according to claim 1 wherein A is substituted with one or more groups as defined in claim 1 and the wavy line means the point of attachment of the ring to the adjacent nitrogen.
から選択される環系であり、
Aが請求項1に記載される一又は複数の基で置換されており、波線が環と隣接窒素の結合の点を意味する、請求項1〜2の何れかに記載の使用のための化合物。 A is
A ring system selected from
A compound for use according to any of claims 1-2, wherein A is substituted with one or more groups as claimed in claim 1 and the wavy line means the point of attachment of the ring to the adjacent nitrogen. .
(式中、R1及びR1’が独立に、H、CF3、NH2、メチル、エチル、F、Cl、Br、I及びOHから選択される;但し、R1がHである場合、R1’はHと異なり、逆もまた同様であり;
Aが請求項1〜4の何れか一項に記載される通りである)
を有することを特徴とする、請求項1〜4の何れかに記載の使用のための化合物もしくはその塩、又はその立体異性型の何れか又はこれらの混合物。 General formula Ia of the following
Wherein R 1 and R 1 ′ are independently selected from H, CF 3 , NH 2 , methyl, ethyl, F, Cl, Br, I and OH; provided that when R 1 is H, R 1 ′ is different from H and vice versa;
A is as described in any one of claims 1 to 4)
A compound for use according to any one of claims 1 to 4, or a salt thereof, or a stereoisomeric form thereof, or a mixture thereof, characterized in that
前記環系を形成する前記環の各々が、
5〜7員を有し、各員は独立に、C、N、O、S、CH、CH2、NHから選択され、
飽和、部分不飽和又は芳香族であり;
AがH、F、Cl、Br、I、ニトロ、シアノ、メチル、エチル、n−プロピル、i−プロピル、n−ブチル、t−ブチル、−CF3、−CH2CF3、直鎖もしくは分枝(C2〜C6)アルケニル、−OH、−OCH3、−OCH2CH3、−COH、−COCH3、−COOH、−COOCH3、−COOCH2CH3、−OC(O)H、−OC(O)CH3、−C(O)NH2、−NH2、−NHCH3、−N(CH3)2、−CH2NH2、−CH2NHCH3、−SH2、−SO−CH3、−SO2−CH3、−SO2NH2、−SO2NHCH3、−SO2NHCH2CH3、−SO2N(CH3)2、−SO2N(CH2CH3)2、−SO2N(CH2CH2CH3)2、−SO2N(CH2CH2CH2CH3)2及び−SO2N(CH2CH2(CH3)2)2からなる群から選択される一又は複数の基で置換されている、請求項5に記載の使用のための化合物。 A is one group of a known heterocyclic ring system having 1 to 2 rings;
Each of the rings forming the ring system is
Has a 5- to 7-membered, independently each member is selected C, N, O, S, CH, from CH 2, NH,
Saturated, partially unsaturated or aromatic;
A is H, F, Cl, Br, I, nitro, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, —CF 3 , —CH 2 CF 3 , linear or minute branch (C 2 ~C 6) alkenyl, -OH, -OCH 3, -OCH 2 CH 3, -COH, -COCH 3, -COOH, -COOCH 3, -COOCH 2 CH 3, -OC (O) H, -OC (O) CH 3, -C (O) NH 2, -NH 2, -NHCH 3, -N (CH 3) 2, -CH 2 NH 2, -CH 2 NHCH 3, -SH 2, -SO -CH 3, -SO 2 -CH 3, -SO 2 NH 2, -SO 2 NHCH 3, -SO 2 NHCH 2 CH 3, -SO 2 N (CH 3) 2, -SO 2 N (CH 2 CH 3 ) 2, -SO 2 N (CH 2 CH 2 H 3) 2, with -SO 2 N (CH 2 CH 2 CH 2 CH 3) 2 and -SO 2 N (CH 2 CH 2 (CH 3) 2) one or more groups selected from the group consisting of 2 6. A compound for use according to claim 5, which is substituted.
N−(4−エチル−6−メチルピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(2);
N−(4−メチル−6−プロピルピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(3);
N−(4−イソプロピル−6−メチルピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(4);
N−(4−ブチル−6−メチルピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(5);
N−(4−tert−ブチル−6−メチルピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(6);
N−(4,6−ジアミノピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(7);
N−(4,6−ジクロロピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(8);
N−(4,6−ジフルオロピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(9);
N−[4−メチル−6−(トリフルオロメチル)ピリミジン−2−イル]−N’−[2−(トリフルオロメチル)フェニル]グアニジン(10);
N−(4−シアノ−6−メチルピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(11);
N−(5−メチルピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(12);
N−(4−クロロ−6−メチルピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(13);
N−(4−フルオロ−6−メチルピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(14);
N−(4−フルオロピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(15);
N−(5−フルオロピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(16);
N−[4,6−ビス(トリフルオロメチル)ピリミジン−2−イル]−N’−[2−(トリフルオロメチル)フェニル]グアニジン(17);
N−(4,6−ジシアノピリミジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(18);
N−ピリジン−2−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(19);
N−ピリジン−3−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(20);
N−ピリジン−4−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(21);
N−ピリミジン−4−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(22);
N−ピリミジン−5−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(23);
N−(4,6−ジメチルピリジン−2−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(24);
N−(3,5−ジメチルフェニル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(25);
N−(2,6−ジメチルピリジン−4−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(26);
N−フェニル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(27);
2−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジメチルベンゼンスルホンアミド(28);
2−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジエチルベンゼンスルホンアミド(29);
2−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジプロピルベンゼンスルホンアミド(30);
2−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジブチルベンゼンスルホンアミド(31);
3−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジメチルベンゼンスルホンアミド(32);
3−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジエチルベンゼンスルホンアミド(33);
3−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジプロピルベンゼンスルホンアミド(34);
3−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジブチルベンゼンスルホンアミド(35);
4−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジメチルベンゼンスルホンアミド(36);
4−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジエチルベンゼンスルホンアミド(37);
4−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジプロピルベンゼンスルホンアミド(38);
4−[(イミノ{[2−(トリフルオロメチル)フェニル]アミノ}メチル)アミノ]−N,N−ジブチルベンゼンスルホンアミド(39);
N−(2−ニトロフェニル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(40);
N−(3−ニトロフェニル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(41);
N−(4−ニトロフェニル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(42);
N−2−チエニル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(43);
N−3−チエニル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(44);
N−1H−ピロール−2−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(45);
N−1H−ピロール−3−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(46);
N−2−フリル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(47);
N−3−フリル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(48);
N−1,3−オキサゾール−2−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(49);
N−1,3−チアゾール−2−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(50);
N−1H−イミダゾール−2−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(51);
N−イソキサゾール−5−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(52);
N−1H−ベンズイミダゾール−2−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(53);
N−(3,4−ジメチルイソキサゾール−5−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(54);
N−(2−アミノフェニル)−N’−(4,6−ジメチルピリミジン−2−イル)グアニジン(55);
N−(4,6−ジメチルピリミジン−2−イル)−N’−(3−エチルフェニル)グアニジン(56);
1−(4−(4−アミノ−2−メチルキノリン−7−イルアミノ)ピリミジン−2−イル)−3−(2−(トリフルオロメチル)フェニル)グアニジン(57);
N−(4−アミノ−2−メチルキノリン−7−イル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(58);
N−キノリン−7−イル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(59);
N−メチル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(60);
N−エチル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(61);
N−プロピル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(62);
N−ブチル−N’−[2−(トリフルオロメチル)フェニル]グアニジン(63);
N−(2−メチルフェニル)−N’−[2−(トリフルオロメチル)フェニル]グアニジン(64);及び
N−[4,6−ビス(メチル)ピリミジン−2−イル]−N’−[2−(トリフルオロメチル)フェニル]グアニジン(65)
から選択される、請求項1〜8の何れかに記載の使用のための化合物。 N-pyrimidin-2-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (1);
N- (4-ethyl-6-methylpyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (2);
N- (4-methyl-6-propylpyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (3);
N- (4-isopropyl-6-methylpyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (4);
N- (4-butyl-6-methylpyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (5);
N- (4-tert-butyl-6-methylpyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (6);
N- (4,6-diaminopyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (7);
N- (4,6-dichloropyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (8);
N- (4,6-difluoropyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (9);
N- [4-Methyl-6- (trifluoromethyl) pyrimidin-2-yl] -N ′-[2- (trifluoromethyl) phenyl] guanidine (10);
N- (4-cyano-6-methylpyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (11);
N- (5-methylpyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (12);
N- (4-chloro-6-methylpyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (13);
N- (4-fluoro-6-methylpyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (14);
N- (4-fluoropyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (15);
N- (5-fluoropyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (16);
N- [4,6-bis (trifluoromethyl) pyrimidin-2-yl] -N ′-[2- (trifluoromethyl) phenyl] guanidine (17);
N- (4,6-dicyanopyrimidin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (18);
N-pyridin-2-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (19);
N-pyridin-3-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (20);
N-pyridin-4-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (21);
N-pyrimidin-4-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (22);
N-pyrimidin-5-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (23);
N- (4,6-dimethylpyridin-2-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (24);
N- (3,5-dimethylphenyl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (25);
N- (2,6-dimethylpyridin-4-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (26);
N-phenyl-N ′-[2- (trifluoromethyl) phenyl] guanidine (27);
2-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-dimethylbenzenesulfonamide (28);
2-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-diethylbenzenesulfonamide (29);
2-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-dipropylbenzenesulfonamide (30);
2-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-dibutylbenzenesulfonamide (31);
3-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-dimethylbenzenesulfonamide (32);
3-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-diethylbenzenesulfonamide (33);
3-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-dipropylbenzenesulfonamide (34);
3-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-dibutylbenzenesulfonamide (35);
4-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-dimethylbenzenesulfonamide (36);
4-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-diethylbenzenesulfonamide (37);
4-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-dipropylbenzenesulfonamide (38);
4-[(imino {[2- (trifluoromethyl) phenyl] amino} methyl) amino] -N, N-dibutylbenzenesulfonamide (39);
N- (2-nitrophenyl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (40);
N- (3-nitrophenyl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (41);
N- (4-nitrophenyl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (42);
N-2-thienyl-N ′-[2- (trifluoromethyl) phenyl] guanidine (43);
N-3-thienyl-N ′-[2- (trifluoromethyl) phenyl] guanidine (44);
N-1H-pyrrol-2-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (45);
N-1H-pyrrol-3-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (46);
N-2-furyl-N ′-[2- (trifluoromethyl) phenyl] guanidine (47);
N-3-furyl-N ′-[2- (trifluoromethyl) phenyl] guanidine (48);
N-1,3-oxazol-2-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (49);
N-1,3-thiazol-2-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (50);
N-1H-imidazol-2-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (51);
N-isoxazol-5-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (52);
N-1H-benzimidazol-2-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (53);
N- (3,4-dimethylisoxazol-5-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (54);
N- (2-aminophenyl) -N ′-(4,6-dimethylpyrimidin-2-yl) guanidine (55);
N- (4,6-dimethylpyrimidin-2-yl) -N ′-(3-ethylphenyl) guanidine (56);
1- (4- (4-amino-2-methylquinolin-7-ylamino) pyrimidin-2-yl) -3- (2- (trifluoromethyl) phenyl) guanidine (57);
N- (4-amino-2-methylquinolin-7-yl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (58);
N-quinolin-7-yl-N ′-[2- (trifluoromethyl) phenyl] guanidine (59);
N-methyl-N ′-[2- (trifluoromethyl) phenyl] guanidine (60);
N-ethyl-N ′-[2- (trifluoromethyl) phenyl] guanidine (61);
N-propyl-N ′-[2- (trifluoromethyl) phenyl] guanidine (62);
N-butyl-N ′-[2- (trifluoromethyl) phenyl] guanidine (63);
N- (2-methylphenyl) -N ′-[2- (trifluoromethyl) phenyl] guanidine (64); and N- [4,6-bis (methyl) pyrimidin-2-yl] -N ′-[ 2- (Trifluoromethyl) phenyl] guanidine (65)
9. A compound for use according to any of claims 1-8, selected from:
の化合物もしくはその塩、又はその立体異性型の何れか又はこれらの混合物
(式中、
Aが1〜2個の環を有する既知の炭素環又は複素環系の一つの基であり、
前記環系を形成する前記環の各々が、
5〜7員を有し、各員が独立に、C、N、O、S、CH、CH2、NHから選択され、
飽和、部分不飽和又は芳香族であり;
AがH、F、Cl、Br、I、ニトロ、シアノ、メチル、エチル、n−プロピル、i−プロピル、n−ブチル、t−ブチル、−CF3、−CH2CF3、直鎖もしくは分枝(C2〜C6)アルケニル、−OH、−OCH3、−OCH2CH3、−COH、−COCH3、−COOH、−COOCH3、−COOCH2CH3、−OC(O)H、−OC(O)CH3、−C(O)NH2、−NH2、−NHCH3、−N(CH3)2、−CH2NH2、−CH2NHCH3、−SH2、−SO−CH3、−SO2−CH3、−SO2NH2、−SO2NHCH3、−SO2NHCH2CH3、−SO2N(CH3)2、−SO2N(CH2CH3)2、−SO2N(CH2CH2CH3)2、−SO2N(CH2CH2CH2CH3)2及び−SO2N(CH2CH2(CH3)2)2からなる群から選択される一又は複数の基で置換されおり;
但し、前記化合物がN−(4−メチル−6−ヒドロキシ−ピリミジン−2−イル)−N’−(2−トリフルオロメチルフェニル)グアニジン、N−[4,6−ビス(メチル)ピリミジン−2−イル]−N’−[2−(トリフルオロメチル)フェニル]グアニジン又はN−[(4−メチル)ピリミジン−2−イル]−N’−[2−(トリフルオロメチル)フェニル]グアニジン以外である)。 Formula (II)
Or a salt thereof, or a stereoisomeric form thereof or a mixture thereof (wherein
A is one group of a known carbocyclic or heterocyclic ring system having 1 to 2 rings,
Each of the rings forming the ring system is
Has a 5- to 7-membered, in each member is independently selected C, N, O, S, CH, from CH 2, NH,
Saturated, partially unsaturated or aromatic;
A is H, F, Cl, Br, I, nitro, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, —CF 3 , —CH 2 CF 3 , linear or minute branch (C 2 ~C 6) alkenyl, -OH, -OCH 3, -OCH 2 CH 3, -COH, -COCH 3, -COOH, -COOCH 3, -COOCH 2 CH 3, -OC (O) H, -OC (O) CH 3, -C (O) NH 2, -NH 2, -NHCH 3, -N (CH 3) 2, -CH 2 NH 2, -CH 2 NHCH 3, -SH 2, -SO -CH 3, -SO 2 -CH 3, -SO 2 NH 2, -SO 2 NHCH 3, -SO 2 NHCH 2 CH 3, -SO 2 N (CH 3) 2, -SO 2 N (CH 2 CH 3 ) 2, -SO 2 N (CH 2 CH 2 H 3) 2, with -SO 2 N (CH 2 CH 2 CH 2 CH 3) 2 and -SO 2 N (CH 2 CH 2 (CH 3) 2) one or more groups selected from the group consisting of 2 Has been replaced;
However, the compound is N- (4-methyl-6-hydroxy-pyrimidin-2-yl) -N ′-(2-trifluoromethylphenyl) guanidine, N- [4,6-bis (methyl) pyrimidine-2 Other than -yl] -N '-[2- (trifluoromethyl) phenyl] guanidine or N-[(4-methyl) pyrimidin-2-yl] -N'-[2- (trifluoromethyl) phenyl] guanidine is there).
5〜7員を有し、各員が独立に、C、N、O、S、CH、CH2、NHから選択され、
飽和、部分不飽和又は芳香族であり;
AがH、F、Cl、Br、I、ニトロ、シアノ、メチル、エチル、n−プロピル、i−プロピル、n−ブチル、t−ブチル、−CF3、−CH2CF3、直鎖もしくは分枝(C2〜C6)アルケニル、−OH、−OCH3、−OCH2CH3、−COH、−COCH3、−COOH、−COOCH3、−COOCH2CH3、−OC(O)H、−OC(O)CH3、−C(O)NH2、−NH2、−NHCH3、−N(CH3)2、−CH2NH2、−CH2NHCH3、−SH2、−SO−CH3、−SO2−CH3、−SO2NH2、−SO2NHCH3、−SO2NHCH2CH3、−SO2N(CH3)2、−SO2N(CH2CH3)2、−SO2N(CH2CH2CH3)2、−SO2N(CH2CH2CH2CH3)2及び−SO2N(CH2CH2(CH3)2)2からなる群から選択される一又は複数の基で置換されおり;
但し、化合物がN−(4−メチル−6−ヒドロキシ−ピリミジン−2−イル)−N’−(2−トリフルオロメチルフェニル)グアニジン、N−[4,6−ビス(メチル)ピリミジン−2−イル]−N’−[2−(トリフルオロメチル)フェニル]グアニジン又はN−[(4−メチル)ピリミジン−2−イル]−N’−[2−(トリフルオロメチル)フェニル]グアニジン以外である、請求項11に記載の化合物。 A is a heterocyclic ring system having 1 to 2 rings, and each of the rings forming the ring system is
Has a 5- to 7-membered, in each member is independently selected C, N, O, S, CH, from CH 2, NH,
Saturated, partially unsaturated or aromatic;
A is H, F, Cl, Br, I, nitro, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, —CF 3 , —CH 2 CF 3 , linear or minute branch (C 2 ~C 6) alkenyl, -OH, -OCH 3, -OCH 2 CH 3, -COH, -COCH 3, -COOH, -COOCH 3, -COOCH 2 CH 3, -OC (O) H, -OC (O) CH 3, -C (O) NH 2, -NH 2, -NHCH 3, -N (CH 3) 2, -CH 2 NH 2, -CH 2 NHCH 3, -SH 2, -SO -CH 3, -SO 2 -CH 3, -SO 2 NH 2, -SO 2 NHCH 3, -SO 2 NHCH 2 CH 3, -SO 2 N (CH 3) 2, -SO 2 N (CH 2 CH 3 ) 2, -SO 2 N (CH 2 CH 2 H 3) 2, with -SO 2 N (CH 2 CH 2 CH 2 CH 3) 2 and -SO 2 N (CH 2 CH 2 (CH 3) 2) one or more groups selected from the group consisting of 2 Has been replaced;
However, the compound is N- (4-methyl-6-hydroxy-pyrimidin-2-yl) -N ′-(2-trifluoromethylphenyl) guanidine, N- [4,6-bis (methyl) pyrimidine-2- Yl] -N ′-[2- (trifluoromethyl) phenyl] guanidine or N-[(4-methyl) pyrimidin-2-yl] -N ′-[2- (trifluoromethyl) phenyl] guanidine 12. A compound according to claim 11 .
(式中、A、R1及びR1’は請求項1に記載される通りである)。 A process for preparing a compound of formula I according to claim 1 comprising reacting an aniline of formula (III) with a cyanamide of formula (IV):
(Wherein A, R 1 and R 1 ′ are as described in claim 1).
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